


Destiel Office AU

by Destiel_is_the_bestiel



Series: Destiel One shots [6]
Category: Supernatural, destiel - Fandom
Genre: AU, Alternate Universe - Human, Angst, CEO Dean Winchester, Destiel - Freeform, First Time, Fluff, Love, M/M, Marriage Proposal, Secretary Castiel, Smut, Teasing, happiness
Language: English
Status: Completed
Published: 2018-11-05
Updated: 2018-11-06
Packaged: 2019-08-18 20:21:10
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,445
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16523975
Author URL: https://archiveofourown.org/users/Destiel_is_the_bestiel/pseuds/Destiel_is_the_bestiel
Summary: The prompt is: CEO Dean wanted his secretaryCastiel's attention, but no matter what he did, the guy didn't show any interest in him at all. The thing is Cas did notice what Dean wanted from him, he just tried to play hard to get in order to make sure that Dean really wanted him for a good, solid relationship and not just for one night stands. In short, Cas made Dean feel jealous by talking, touching the other guys at work but him for a whole month xD. I hope a smut scene can be included in this too if you're up for it and I really love bottomCas :P.





	1. Chapter 1

**Author's Note:**

  * For [Maybelene](https://archiveofourown.org/users/Maybelene/gifts).



> This prompt was recommended to me and I did it.

Dean Winchester is the CEO of Men of Letters Corporations, they are one of the largest mailing companies, right up there with UPS and FedEx. Dean is 29 years old and in charge of his department, filing. His personal secretary is Castiel Novak, a 26 year old man. His coworkers are Charlie, a very smart I.T woman and Sam Smith, a 22 year old, and Cas’ best friend. 

 

Dean walked by Castiel’s desk and stood next to it, he saw the gorgeous blue eyes look up at him, 

 

    “Hello Dean, is there anything you need?” 

 

Oh god, Castiel is such a dork, “Castiel, I was just… Can you make me some copies of these papers, thanks.” Dean quickly turned and walked away, his face red.  _ Goddammit, he’s my secretary, he probably doesn’t even like me. _ Dean was thinking as he walked away.

 

Cas stood up and walked to the copier, he was thinking about Dean as he worked,  _ This man is a player, I can’t get in a relationship with him, he’ll just hurt me.  _ Cas sighed as he walked back to his desk, papers in hands. He sat down and a though hit him,  _ What if I test him.  _ He decided to play hard to get, Cas walked over to Sam and whispered in his ear,

 

    “Hey Sam, is it okay if I ‘flirt’ with you, I want to see if Dean is serious about me.” 

 

Cas knew that Sam understood him, Sam was the one he confided in about everything, Sam was also the one who told Cas that Dean likes him, even if Cas didn’t believe him at first. 

 

    “So, you’re finally gonna act on your feelings. Sure, go ahead.” Cas rested his chin on Sam’s head and reached over, he spoke up loud enough for Dean to hear, but not too loud that it sounds like he wants him to hear, “So, Sam, wanna come over for dinner tomorrow night?” Cas said it in his flirtiest tone.

 

Dean heard Castiel talking with Sam, so he decided to eavesdrop. When he heard what Cas said, he froze, he didn’t want Cas to be with Sam, he wanted to be with Cas. Dean decided that he needed to act soon.

 

Sam spoke up, “Sure Cas, I’ll come over, 9 o’clock?” Cas smiled, thankful for Sam, he leant down and whispered into Sam’s ear, “Thanks Sam.” Cas turned and walked past a gaping Dean, 

    “Oh, Dean, the copies are on my desk, I’ll go grab them.” Cas told him, awkwardly

 

Dean blinked, confused, “Oh, it’s okay, I’ll go grab them.” Dean rushed over and walked to Cas’ desk and picked up the stack of papers. Dean walked over to Charlie’s office, and closed the door behind him, he leant his back on the door, “Charlie, I need some help, please.” Charlie stood up from her desk and walked over to Dean,

 

    “Dean, what’s wrong? Is this about Castiel?” Dean squeezed his eyes shut, he let out a reply “Don’t even say his name, he- he invited Sam over for dinner tomorrow night, I- I should have made a move earlier, it’s too late now.” Charlie wrapped her arms around Dean’s shoulders, “Dean, you still have a chance, now, I haven’t dated a guy since 2004, but I can see the way he acts around you, it’s how I acted around Dorothea when I first met her.” Charlie looked down at the ring on her finger and smiled.

 

Dean thanked Charlie and left her office and went to his. Cas was already sitting in his usual seat when Dean entered, “Hello Dean, ready for work?” Dean sighed and sat down, “Yep, let’s do this.” The day went by fairly quickly, Dean kept sneaking looks at Cas, who kept pretending not to notice. 

 

When the day was over, Cas walked back out to the main office space. He went over to Balthazar and placed a note on his desk, making sure that Dean noticed, the note only had scribbles on it, and Balthazar didn’t care, but Dean noticed. He walked over to Cas’ desk and wrote on a piece of paper, ‘ _ Castiel, please come to my office before you leave.’  _ Dean went back to his office and sat in his chair, his leg started bouncing nervously, he just stared at the door, waiting.

 

Castiel saw the note on his desk, the worst case scenario ran through his head,  _ Is Dean going to fire me because of the flirting? I’ll have to apologize.  _

 

Cas opened the door and Dean straightened up in his seat, “Hey-um hey Cas.” He said a bit to enthusiastically. Cas took a seat, “Dean, did I do something wrong?” Dean looked at him apologetically,

 

    “Of course not, I was just hoping to ask you on a date?” Dean said with a hint of desperation, Cas heaved a sigh of relief and smiled, “I would love that.” Dean smiled widely and stood up, “You would?” He took Cas hands in his and looked into his eyes. Cas leant forward and then pulled back and placed his fingers in front of Dean’s lips, “Tomorrow night sound good?” Dean pulled back, “Sounds perfect.” Cas walked out of the office and packed up his items and left the building.

  
  
  


Date Night

  
  


Dean was getting ready for his date, he couldn’t decide what to wear. He was pacing back and forth, there was at least 4 outfits on his bed. Eventually he decided on a blue dress shirt and black slacks. He drove to the restaurant that he and Cas decided upon, it was a fancy steak place. He entered the restaurant and went to the front area, “Hello, I have a reservation for two, under the name Winchester.” Dean looked at the ground nervously, worried that Castiel might have decided against showing up. 

    “Oh, yes, there is a young man sitting over at that table, a waiter will be with you shortly.” Dean breathed a breath of relief. He walked over to the table where Cas was seated, “Hi Cas, sorry that I was late.” Cas gave him a side smile, “You aren’t, I just showed up early.” Dean chuckled at those words. He looked up into Castiel’s eyes, they were so blue, so deep. “Cas, yo-your eyes are so beautiful, sorry I don’t want to sound creepy.” Dean looked down at his hands and started twiddling his thumbs until Cas placed his hands on top,

    “Dean, thank you, no one has ever said anything like that before.” He looked down at the table as a tear rolled off his cheek. Dean tensed up and reached a hand up to wipe away Cas’ tear, “Cas’ what’s wrong?” Cas looked down, sniffled quietly and then responded, “It-It’s nothing, just thinking of something from my past.” Dean’s smile faded, “Cas, you can tell me, you don’t have to, but you can.” Cas looked into Dean’s eyes and instantly felt calmed,

 

    “Okay Dean. Well, a few years ago I was in a relationship, it was with another man, Zachariah. We were together for a few years, but he didn’t love me.” Cas paused and took a deep breath, “He was abusive, always telling me that he’s my only choice, nobody would love me, besides him. Eventually he got physical, he would push me around, then at one point, he-he-” Dean squeezed Cas’ hands and then spoke up, “Cas, you don’t have to tell me if you don’t want to, I don’t want to make you uncomfortable.” Cas looked down, “I’ll tell you after we finish dinner, I just need to compose myself, I’m sorry.” 

Dean’s shot Cas a soft smile, “Cas, I promise, it’s perfectly fine.” “Thank you Dean.” They ordered their meals and ate, having casual conversation. After they finished their food they went to outside, it was late and there was almost nobody around. Cas took Dean’s hand and turned to him, “Dean, I’m ready to tell you.” Dean squeezed his hand, “Okay Cas.”

    “Zachariah eventually caught me talking with another man online, it wasn’t even romantic, we were just talking, but Zach got jealous so he threw my phone against the concrete outside and pushed me down the stairs of our house. The fall broke my left arm, fractured a part of my spine, and a piece of the railing impaled my right shoulder blade.” Cas motioned to his shoulder, “I have a huge scar.” Cas scoffed, “Do you wanna see it?” Dean placed his hand on Castiel’s shoulder, “You don’t have to show me if you don’t want to.” Cas smiled at Dean, warmly. Cas turned around and pulled his shirt over his head.

 

Once his shirt was off, Dean could see a healed gash on Cas’ back. He reached his hand up and ran his thumb over the scar, and tensed up, he hated the thought of somebody hurting Castiel, “Cas, how long ago was this?” Cas turned around to face Dean, “It was about 2 years ago. After the incident I decided to go to the police, they arrested him and I got a restraining order on him, he’s gonna be in jail for about 3 more years.” Dean saw tears forming in Castiel’s eye. He reached up and wiped away the tear, “Cas, I promise that I won’t ever hurt you, but I understand if you don’t want to start a relationship.” Cas cupped Dean’s cheek, “Dean, I would love to date you, if that’s what you’re asking.” Dean smiled and leaned into Cas’ touch. He reached his hand behind Cas’ neck and brought their faces together, briefly pressing lips together, softly. Cas pressed into it, surprising Dean, who returned the kiss. Cas pulled away and rested his head on Dean’s shoulder, “Thank you Dean.”

 

Cas decided that he wanted to work at another company, so he applied to Flight Enterprise, where he got accepted as a business analyst. Dean continued as a CEO at Men of Letters Corps. Dean and Cas have been dating for about 2 years and are now going on a date at Dean’s house.

 

Cas knocked on Dean’s door and heard shuffling around inside then a “Come in” When he opened the door, he saw Dean standing there with a bundle of roses in his hands. Dean sent him a bright smile, “Hey Cas.” Cas walked up to his boyfriend and planted a soft kiss on his cheek, then on his lips, when he pulled away, Dean was looking down at him, “C’mon Cas, let’s watch a movie. I made popcorn!” Dean was excited and nervous at the same time. Dean handed the flowers to Cas and pulled him into the living room.

 

The men both sat on the couch, Dean had his arm wrapped around Castiel’s shoulders, resting on his right arm. They decided to watch the first Star Wars movie. While Cas was watching the movie, Dean was watching Cas, all his little reactions were adorable. The movie ended quicker than it started, then Dean felt panicked. He looked over to Cas and gave him a soft little squeeze. 

 

Cas could tell that something was wrong, by looking at his face, he sat up, “Dean what’s wrong?” Dean stiffened up, 

 

    “Nothing’s wrong Cas, but I do want to talk to you.” Cas instantly became worried, “Cas, I really like you, and I wanted to tell you. I- I love you Cas.” Cas’ eyes started watering, “Cas, I was hoping that you would like to...move in with me?” Cas couldn’t even speak, so he didn’t. He covered his mouth and just started crying and nodding his head frantically. Dean grabbed the back of Cas’ neck and brought him in for a kiss quickly. Cas pulled away, 

 

    “Dean, I love you too” Dean was shocked at the words, he didn’t want to rush Cas, “Cas, are you sure? I don’t want you to feel rushed.” Cas replied by pulling Dean in for another kiss, briefly, “Dean, I do love you, and I want to move in with you. You aren’t rushing me, you could never make me feel that way.” 

 

Cas moved in a few days later, with Dean’s help, later that night they were laying in bed. Dean placed a hand on Cas’ cheek and pressed their lips together, Cas replied by climbing on top of Dean. Dean wrapped his arms around Cas’ back, Dean pulled his mouth away, “Cas, I love you so much.” Cas rolled off of Dean and Dean wrapped his arm around Cas’ shoulders, “I love you too Dean, you are the most important person in my entire life.” That night, Cas fell asleep in his boyfriends arms.

 

Dean and Castiel have been dating for about 6 years, and living together for 4. They have yet to actually make love, not because they didn’t love each other, they just both weren’t ready. Cas decided that he wanted to further their relationship so he went to the jewelry store to purchase a surprise for Dean. When he got back to the house, he saw Dean sitting on the couch, watching TV. “Hey Dean, can you do something for me?” Dean turned to Cas and replied, “Of course.” Cas reached for Dean’s hand and tugged it along with him, “Follow me.” Cas told him. Dean obliged.

 

Cas held Dean’s hand and led him outside, it was autumn and there was red, orange, and yellow leaves scattered on the ground. The crunching under their feet made Cas assume that Dean already knew where they were. Cas pulled a black box out of his pocket and hid it behind his back, “Dean, open your eyes.” 

 

Dean opened his eyes and saw Cas standing in front of him, then the leaves under his feet, he was almost speechless, “Cas this is beautiful.” Cas slowly went down on one knee, Dean pressed his hands on his mouth and started crying, “Dean, I’ve loved you for so long, I would like to know if you would do the honor of being my husband?” Cas was grinning at Dean, hope in his eyes, but Dean could barely see that, his vision was blurred by tears, but he was frantically nodding, he fell down onto his knees and wrapped his arms around Cas, pulling his close he kept repeating the same 3 phrases “Yes” “of course” and “I love you” Cas leant into the hug and then pulled back, he took Dean’s left hand in his and slid the ring onto Dean’s ring finger. 

 

Dean’s breath hitched as he felt the ring slide on, he was finally engaged to the man of his dreams. Dean pulled Cas’ face up to his and kissed at his lips. The men were pushing and pulling against each other, neither wanting to stop. Eventually Dean stood up, but didn’t break the kiss, pulling Cas along with him, he kept his left hand in Cas’ right, pulling him back to the house, to their bedroom. 

 

Dean laid Cas down on the bed and climbed on top of him, he started pulling his shirt over his head then paused, “Cas, do you want to do this? We don’t have to if you don’t want to.” Cas pulled Dean’s shirt off, then looked right into his eyes before responding, “I’m want this Dean, I want you, all of you.” That was all Dean needed to hear, he hungrily attacked Cas’ lips, he reached down and reached down to his pants, unbuttoning and unzipping. He pulled off Castiel’s pants and continued kissing him. Cas returned the favor and removed Dean’s. 

 

Dean pulled away for a moment, “Give me a moment Cas, we need something.” Dean stood and left the room, leaving Cas alone in the bed, a few moments later, Dean returned with a small bottle in his hands. He climbed back on Cas, slowly pulling off his boxers, Cas responded by reaching down and removing Deans, quickly revealing his swollen cock, excited to make love to his fiance. God, that word makes Cas’ stomach roll with happiness. Cas knew what Dean was doing, and he was completely ready and willing to let Dean in him. Dean finished removing Cas’ boxers. Dean opened the bottle of lube and squeezed a generous amount of onto his fingers, he pulled his face away and looked Cas in the eyes, “Cas, are you ready?” Cas wrapped his fingers around the back of Dean’s neck and pulled him in for a wet kiss, when he pulled away, it left a string of spit connecting their mouths, “Dean, I’ve always been ready.”

 

Dean took his lubricated fingers and rubbed them around Cas’ puckered hole. Feeling it tense up, he slowly pressed a finger into it, it was warm and tight, so Dean slowly added a second finger, spreading the lube. A moment later he removed the fingers, much to Cas’ despair. Dean gripped his own cock and spread the lube over it, making it harden even more. Dean slowly pressed into Cas, hesitantly. Cas felt a pressure and a burning, but not painfully, he pressed down onto Dean, impatiently. Dean slowly thrusted into Cas, afraid to hurt him, but growing more impatient he grabbed Cas and bit his shoulder, leaving a light mark. Cas moaned as Dean bit down. When Dean realized that Cas was okay, he decided he didn’t need to be gentle. He thrust his cock into Cas, surprising him. Dean started moving faster and rougher, brushing against Castiel’s prostate, eliciting a loud moan from him. Dean was so close to cumming and continued faster, all the way in Cas, completely hitting his prostate forcefully, Cas came in between them, a warm sticky mess. Soon Dean couldn’t hold back any longer and released inside Cas’ rectum. Both men were out of breath, Dean pulled his worn out cock out of Cas and cum came flowing out of Cas’ worn out hole. Cas rested his head on Dean’s chest and listened to his heartbeat, slowing back to normal. “Thank you Dean.”


	2. Marriage

**Notes for the Chapter:**

> Someone asked for another chapter, so I wrote it :P

                About 6 months later (AKA Wedding Day)

 

The wedding was on a beach, all of their friends and family showed up. Dean and Cas walked in, joined by their elbows, their steps matching up, striding down the corridor. They slowed to a stop in front of the priest, and turned to face each other. The priest spoke up,

 

    “Dearly beloved, we are gathered here today to join Castiel Novak and Dean Winchester in holy matrimony, by the power vested in me.” The two men turned and held each other's hands. “I believe you two wrote your own vows?” Dean turned to the priest and nodded as he pulled a folded piece of paper out of his coat.

 

    “Cas, I’ve known you for over 7 years, and I’ve loved you the entire time. When we first met, I didn’t think that you were even interested in guys, hell, I didn’t even know that  _ I  _ was into guys, I denied it for years. I would go out drinking and sleeping around with women just to get my mind off of you. When I saw you flirting with other guys in the office, I knew I had a chance, I knew I couldn’t watch you be with another man. That was the best decision I ever made in my entire life, I love you so much.”

 

Cas was shaking while crying, he could barely breath he was so happy, the only thing keeping him grounded was gripping Dean’s hands.

 

    “Dean, it was so difficult being your secretary, not because I didn’t like you, it was the exact opposite, I instantly fell in love with you when I met you, but you were having sex with so many other people. I noticed that you were a little more nervous around me, but I didn’t know if you just wanted me to sleep with, or to love. I started flirting with people in front of you, just to see your reaction, and as they say, the rest is history. Dean, thank you for being my boyfriend, fiance, and now my husband, I love you.”

 

Cas reached up and wiped away the tear slipping down Dean’s face, their moment was interrupted by the priest, “Now, I pronounce you husband and husband, now kiss the groom.” Dean gingerly snuck his hand behind Cas’ neck and his other hand on his waist, he pulled him in and let their lips collide, Dean licked at Cas’ lips and Cas bit his bottom lip. They heard an awkward cough and knew they had been kissing for too long, besides they had the rest of their lives to make up for it.

**Notes for the Chapter:**

> HEYOOOO tell me some headcanons plzzz

**Author's Note:**

> Thank you for reading. This took such a long time to do. Should I add in another chapter like their wedding? LMK


End file.
